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There you are: Standing at the edge of the metaphorical startup cliff. You want to cannonball into the abyss that is Founder-hood… But, you’re scared as hell that you might be jumping in too soon.

What do you do?

Are you asking yourself the right questions? How do you evaluate whether this very moment is the one to take the plunge? Are you sure?

Every startup Founder goes through this inner battle, yet few know what to look for.

While everyone’s situation is unique in their own way, there are three critical indicators that can help you determine if the timing is right— before making the leap.

Critical Indicator #1: Customers are buying — constantly

The moment you start seeing real revenue from a consistent stream of customers, ...

I believe passion is infectious, and when you get likeminded individuals in a room together, discussing real change and impact for not only a company or organization, but also an entire city, it creates a real sense of dedication.

Buenos Aires, Argentina, is not the first place that people think of when they think of startups — but that’s going to change if Lisa Besserman has anything to say about it.

Lisa’s organization, Startup Buenos Aires (SUBA), has been working tirelessly for the past few years to harness and unite the massive amounts of creative energy and technical knowledge that are floating around South America’s most dynamic city.

In just three years, Lisa and her team have not only created a resource hub for entrepreneurs in Bue...

Rich Aberman and his co-Founder Bill Clerico were making great progress with their payment processing startup, WePay.

The platform – which made it easy for small businesses, organizations and nonprofits to accept credit card payments online – had taken shape over the course of six years. Revenue was growing month-over-month. Customers liked it, the press liked it — and investors had put in a lot of money to keep growing it.

But in 2014, Rich and Bill were getting ready to kill it.

The transition away from direct business

No, it wasn’t the startup equivalent of a suicide pact. They hadn’t given up – quite the opposite. Almost without meaning to, they had landed on an opportunity with the potential to leave the direct business in the du...

When preparing for the new year, my partners and I look back on what has worked in our company, and what areas we would like to develop. This year we agreed we would put all commercially-oriented people in one big team — with me in charge.

Great, I thought, let me rethink how to make a commercial team in a way hasn’t been done before.

I Don’t Want to Become Evil Corp

At first, I wanted to organize my teams in a way that didn’t mirror the “Evil Corp”.

I’m not really sure why I was so afraid of this… I guess I’ve seen and heard a lot of stories lately where this has become the situation.

We even have people joining our team from other startups because their old jobs went too corporate, both organization-wise and product-wise. Somewhere along...

Everyone tells aspiring entrepreneurs — especially those in tech — that San Francisco is the only place they can be successful. After building a company in North Dakota and finding all the talent and funding I needed there, I’d like to offer an alternative perspective.

When it comes to small towns, it can be easy to think that the grass is greener somewhere else. There are small-town myths like you can’t find the right talent or you can’t raise funding away from the coasts. There is also a shortage of belief in success in small towns. But common startup concerns aren’t fixed by moving somewhere with more of everything.

In fact, with everyone crammed in the same place, startup necessities from money to quality hires to community ...

Stealth mode startups. They’re the cool kid’s club of the startup world. Who doesn’t want to know the secret, awesome, disruptive company that the latest 22-year old tech hot shot is working on?

Stealth mode is an excellent psychological trick that founders employ with the hope that the even cooler kids — i.e. the venture capitalists — will be intrigued and want to come join their club.

Problem is, it’s kind of BS.

Look, I’m not saying that no founder should ever have a stealth mode startup. There are legitimate reasons to choose to keep things quiet until you feel like your baby is ready for the world.

However, for most startups, the benefits of being out in the open — from finding the right product/market fit to locating your first 100 c...

“Stagnancy isn’t good for anything, from standing pools of water to athletic performance to startups serious about growth. Ensure positive outcomes and superior employee performance and avoid team rifts well in advance by staying attuned to changing individual and cultural needs within your workplace.”

–Michael Manning, How to Know When to Shuffle Your Employee Deck

“Every company needs to set its sights on fostering alignment between the best roles for team members as befits the business’s objectives and vision. It all starts with taking some steps toward a more organic way of managing people,” proclaims Michael Manning in her article on why shifting an employee role may allow you to see your team members in a new light.

Easie...

Software startups, especially in their early stages, can be rough. As a founder, it’s easy to get lost in a world of opportunity. You could build anything — but you need to build just one thing. When you finally figure out what that one thing is, you know that you’re a million iterations away from that magical product/market fit moment.

“It’s interesting because I think there’s an obligation as an entrepreneur to always have to say that we’re killing it—but the reality is always, always, always very different. In the same day you’re taking over the world, then going bankrupt, then taking over the world, and then going bankrupt again. You’re going back and forth between and that low three or four times a day. It’s quite bizarre. Every positi...

Some entrepreneurs sail blissfully into the sunset after their first big payday. Others — like us — can’t imagine anything more boring. Instead, we thrive on constantly risking it all to build something out of nothing.

This condition of serial entrepreneurship is what I call “one and not done” syndrome. Maybe we’re crazy to be willing to start a business again and again. We know it will be hard, if not seemingly impossible, and there will be times when we will be overwhelmed with frustration. In spite of that, we know the journey is worth it.

If you’re this special breed of entrepreneur, I feel both sorry and happy for you. More than anything, I welcome you to the club.

There is a magic to what we do as entrepreneurs. We c...

People say that the co-Founder relationship is like a marriage — but what about when it actually is a marriage?

That’s the case for Michael and Angela Smith. They founded YipYap and created the first Bluetooth-enabled smart phone for kids, Pipsqueak, after realizing that handing over their very expensive phones every time their four kids wanted to talk to Grandma just wasn’t going to work.

“I love — and I’ve told her this — I love doing business with her,” Michael told me over the phone from the house in Texas that he shares with Angela and their kids.

But juggling a successful startup, homeschooling their kids, and still finding time for each other isn’t easy. Things can hectic and it’s a constant balancing act for these life and business ...